Real Estate Investment Properties for Sale in Longwood, FL

Looking for investment property in Longwood, FL with high ROI ?

Explore a variety of short-term homes & houses in Longwood, FL. Invest wisely with VRBO & Longwood, FL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Longwood, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
3996 RADLEY COURT #3996 Longwood, FL Light and bright 2 bedroom, 2 bath condo in the highly desirable Wekiva Hunt Club communit...	2 beds \| 2 baths \| 1,427 sq.ft.	$280,000	Airbnb cash on cash: -1.51% Traditional cash on cash: 3.22% Airbnb Rental Income: $1115 Traditional Rental Income: $1988 Airbnb ROI: -1.51% Traditional ROI: 3.22%
4102 CLUBSIDE DRIVE #4102 Longwood, FL Spacious 2-Bedroom Corner Unit in Clubside at Sabal Point â Private, Updated & Move-In R...	2 beds \| 3 baths \| 1,380 sq.ft.	$232,900	Airbnb cash on cash: -1.29% Traditional cash on cash: 3.95% Airbnb Rental Income: $1115 Traditional Rental Income: $1894 Airbnb ROI: -1.29% Traditional ROI: 3.95%
3235 WINDING PINE TRAIL Longwood, FL Life unfolds beautifully in this golf front estate in the desirable guard gated community ...	4 beds \| 6 baths \| 4,262 sq.ft.	$1,400,000	Airbnb cash on cash: 1.1% Traditional cash on cash: 3.79% Airbnb Rental Income: $5377 Traditional Rental Income: $7787 Airbnb ROI: 1.1% Traditional ROI: 3.79%
211 FAIRWAY DRIVE #211 Longwood, FL Welcome to this charming condo located in the highly sought-after, gated community of The ...	3 beds \| 2 baths \| 1,496 sq.ft.	$187,500	Airbnb cash on cash: 7.73% Traditional cash on cash: 5.4% Airbnb Rental Income: $3221 Traditional Rental Income: $2080 Airbnb ROI: 7.73% Traditional ROI: 5.4%
899 LORMANN CIRCLE Longwood, FL Welcome to your Longwood retreat. Enjoy the peace of mind that comes with no HOA! This me...	3 beds \| 2 baths \| 969 sq.ft.	$289,990	Airbnb cash on cash: 7.38% Traditional cash on cash: 4.84% Airbnb Rental Income: $3221 Traditional Rental Income: $1803 Airbnb ROI: 7.38% Traditional ROI: 4.84%
199 E MARVIN AVENUE Longwood, FL Under contract-accepting backup offers. Come see this spacious, updated First time Homebuy...	3 beds \| 1 baths \| 967 sq.ft.	$265,000	Airbnb cash on cash: 7.76% Traditional cash on cash: 4.53% Airbnb Rental Income: $3221 Traditional Rental Income: $1686 Airbnb ROI: 7.76% Traditional ROI: 4.53%
112 CROWN OAKS WAY #112 Longwood, FL Under contract-accepting backup offers. Huge price reduction . Your gain and owners loss! ...	2 beds \| 2 baths \| 1,119 sq.ft.	$130,000	Airbnb cash on cash: -4.32% Traditional cash on cash: 3.69% Airbnb Rental Income: $1115 Traditional Rental Income: $1741 Airbnb ROI: -4.32% Traditional ROI: 3.69%
2681 AZALEA DRIVE Longwood, FL A Home to Be Thankful For â $10,000 in Buyer Savings! As the season turns and the air...	3 beds \| 2 baths \| 1,399 sq.ft.	$365,000	Airbnb cash on cash: 4.94% Traditional cash on cash: 3.48% Airbnb Rental Income: $3221 Traditional Rental Income: $1994 Airbnb ROI: 4.94% Traditional ROI: 3.48%
364 HOWARD BOULEVARD Longwood, FL Welcome to this charming 3-bedroom, 2-bath home tucked away at the end of a quiet dead-end...	3 beds \| 2 baths \| 1,400 sq.ft.	$370,000	Airbnb cash on cash: 5.33% Traditional cash on cash: 4.26% Airbnb Rental Income: $3221 Traditional Rental Income: $2122 Airbnb ROI: 5.33% Traditional ROI: 4.26%
310 VISTA OAK DRIVE Longwood, FL ~MOTIVATED SELLER~ Welcome to your dream home in the highly sought-after gated community...	4 beds \| 5 baths \| 3,286 sq.ft.	$999,500	Airbnb cash on cash: 2.33% Traditional cash on cash: 3.64% Airbnb Rental Income: $5377 Traditional Rental Income: $5513 Airbnb ROI: 2.33% Traditional ROI: 3.64%
1530 ARDEN STREET Longwood, FL Under contract-accepting backup offers. Fall in love with this beautifully updated 4-bedro...	4 beds \| 2 baths \| 1,840 sq.ft.	$399,000	Airbnb cash on cash: 9.45% Traditional cash on cash: 4.79% Airbnb Rental Income: $5377 Traditional Rental Income: $2551 Airbnb ROI: 9.45% Traditional ROI: 4.79%
561 SHINING ARMOR LANE Longwood, FL Invest with success and buy through Auction.com. This bank-owned investment property is a ...	N/A beds \| N/A baths \| N/A	$358,000	Airbnb cash on cash: 2.29% Traditional cash on cash: 2.71% Airbnb Rental Income: $2039 Traditional Rental Income: $1652 Airbnb ROI: 2.29% Traditional ROI: 2.71%
105 FAIRWAY DRIVE Longwood, FL Stunning 2-Bedroom Condo in Gated Community â Fairway Villas at The Springs! Welcome ...	2 beds \| 1 baths \| 1,140 sq.ft.	$199,999	Airbnb cash on cash: -1.58% Traditional cash on cash: 2.95% Airbnb Rental Income: $1115 Traditional Rental Income: $1600 Airbnb ROI: -1.58% Traditional ROI: 2.95%
449 SPRINGWOOD COURT Longwood, FL This beautifully updated three-bedroom, two-bath home in Longwood offers 1,075 square feet...	3 beds \| 2 baths \| 1,075 sq.ft.	$325,000	Airbnb cash on cash: 5.83% Traditional cash on cash: 3.67% Airbnb Rental Income: $3221 Traditional Rental Income: $1834 Airbnb ROI: 5.83% Traditional ROI: 3.67%
162 DUNCAN TRAIL Longwood, FL Under contract-accepting backup offers. Step into this updated 4-bed, 2-bath home that sit...	4 beds \| 2 baths \| 1,907 sq.ft.	$450,000	Airbnb cash on cash: 8.09% Traditional cash on cash: 3.76% Airbnb Rental Income: $5377 Traditional Rental Income: $2468 Airbnb ROI: 8.09% Traditional ROI: 3.76%
731 CRESTBROOK LOOP Longwood, FL Welcome to 731 Crestbrook Loop in The Landings- one of Longwoodâs most desirable gated ...	3 beds \| 3 baths \| 2,140 sq.ft.	$405,000	Airbnb cash on cash: 4.26% Traditional cash on cash: 6.05% Airbnb Rental Income: $3221 Traditional Rental Income: $3173 Airbnb ROI: 4.26% Traditional ROI: 6.05%
104 N SILVER CLUSTER COURT Longwood, FL Under contract-accepting backup offers. Seller may consider buyer concessions if made in a...	3 beds \| 2 baths \| 1,386 sq.ft.	$395,000	Airbnb cash on cash: 4.51% Traditional cash on cash: 3.41% Airbnb Rental Income: $3221 Traditional Rental Income: $2089 Airbnb ROI: 4.51% Traditional ROI: 3.41%
203 WEEPING ELM LANE Longwood, FL Under contract-accepting backup offers. Nestled in Longwoodâs guard-gated Springs commun...	2 beds \| 3 baths \| 1,816 sq.ft.	$465,000	Airbnb cash on cash: -0.46% Traditional cash on cash: 3.41% Airbnb Rental Income: $1115 Traditional Rental Income: $2425 Airbnb ROI: -0.46% Traditional ROI: 3.41%
2040 E TRIANGLE DRIVE Longwood, FL NEW PRICE REDUCTION! Now priced below market value. Charming, Updated 3-Bedroom Home ...	3 beds \| 2 baths \| 1,283 sq.ft.	$345,000	Airbnb cash on cash: 5.42% Traditional cash on cash: 3.62% Airbnb Rental Income: $3221 Traditional Rental Income: $1912 Airbnb ROI: 5.42% Traditional ROI: 3.62%
1889 RANCHLAND TRAIL Longwood, FL Exquisite 4-Bedroom Estate with Pool on 2+ Acres in the Coveted LongwoodâLake Mary Area,...	4 beds \| 3 baths \| 2,333 sq.ft.	$989,000	Airbnb cash on cash: 2.96% Traditional cash on cash: 1.83% Airbnb Rental Income: $5377 Traditional Rental Income: $3252 Airbnb ROI: 2.96% Traditional ROI: 1.83%
100 MARCY BOULEVARD Longwood, FL Under contract-accepting backup offers. Welcome to 100 Marcy Blvd, a stunning home in the ...	4 beds \| 3 baths \| 2,460 sq.ft.	$625,000	Airbnb cash on cash: 5.59% Traditional cash on cash: 4.28% Airbnb Rental Income: $5377 Traditional Rental Income: $3526 Airbnb ROI: 5.59% Traditional ROI: 4.28%
4 WOODEN SHOE LANE Longwood, FL Under contract-accepting backup offers. Short Sale. Must See 4 bed, 2 bath home in the est...	4 beds \| 2 baths \| 2,682 sq.ft.	$350,000	Airbnb cash on cash: 9.51% Traditional cash on cash: 5.03% Airbnb Rental Income: $5377 Traditional Rental Income: $2819 Airbnb ROI: 9.51% Traditional ROI: 5.03%
210 BANBURY COURT Longwood, FL Your new pool home in the desirable Wekiva Hills community is waiting for you. This 4 bedr...	4 beds \| 2 baths \| 2,720 sq.ft.	$470,000	Airbnb cash on cash: 8.41% Traditional cash on cash: 5.97% Airbnb Rental Income: $5377 Traditional Rental Income: $3220 Airbnb ROI: 8.41% Traditional ROI: 5.97%
358 WINCHESTER COURT Longwood, FL Under contract-accepting backup offers. Seller Motivated Closing cost, rate buy down ...	3 beds \| 3 baths \| 1,682 sq.ft.	$335,000	Airbnb cash on cash: 3.6% Traditional cash on cash: 2.6% Airbnb Rental Income: $3221 Traditional Rental Income: $2181 Airbnb ROI: 3.6% Traditional ROI: 2.6%
258 W Sabal Palm Place unit: 22 #22 Longwood, FL Enjoy low-maintenance living & a terrific investment opportunity! This stylish 2-bedroom, ...	2 beds \| 2 baths \| 1,202 sq.ft.	$253,000	Airbnb cash on cash: -1.66% Traditional cash on cash: 2.3% Airbnb Rental Income: $1115 Traditional Rental Income: $1688 Airbnb ROI: -1.66% Traditional ROI: 2.3%
150 ESSEX DRIVE Longwood, FL Step into the warmth and charm of this rare cabin-style retreat nestled in the heart of Lo...	3 beds \| 2 baths \| 1,449 sq.ft.	$440,000	Airbnb cash on cash: 3.8% Traditional cash on cash: 3.08% Airbnb Rental Income: $3221 Traditional Rental Income: $2199 Airbnb ROI: 3.8% Traditional ROI: 3.08%
501 RIVERBEND BOULEVARD Longwood, FL Are you ready to finally add the most important key to your keychain? After scrolling for...	4 beds \| 2 baths \| 2,559 sq.ft.	$599,900	Airbnb cash on cash: 5.23% Traditional cash on cash: 2.61% Airbnb Rental Income: $5377 Traditional Rental Income: $2824 Airbnb ROI: 5.23% Traditional ROI: 2.61%
494 N PIN OAK PLACE #302 Longwood, FL Currently this unit is also available as a rental listing at $1,750. Resort-style livi...	2 beds \| 2 baths \| 1,110 sq.ft.	$199,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 6.41% Airbnb Rental Income: $1115 Traditional Rental Income: $1717 Airbnb ROI: 1.24% Traditional ROI: 6.41%
448 VILLAGE VIEW LANE Longwood, FL Step inside this beautifully upgraded Sabal Point home, where classic character meets mode...	5 beds \| 3 baths \| 2,634 sq.ft.	$715,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.16% Airbnb Rental Income: $null Traditional Rental Income: $2938 Airbnb ROI: N/A Traditional ROI: 2.16%
966 N RONALD REAGAN BOULEVARD Longwood, FL HIGH AND DRY! Located just 1/2 mile from the Longwood SunRail Station. Donât miss your o...	5 beds \| 3 baths \| 2,490 sq.ft.	$595,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.32% Airbnb Rental Income: $null Traditional Rental Income: $3535 Airbnb ROI: N/A Traditional ROI: 4.32%
674 PINE SHADOW COURT Longwood, FL Discover this beautifully maintained 4-bedroom, 3-bath home in the sought-after Sabal Poin...	4 beds \| 3 baths \| 2,754 sq.ft.	$710,000	Airbnb cash on cash: 4.75% Traditional cash on cash: 3.41% Airbnb Rental Income: $5377 Traditional Rental Income: $3403 Airbnb ROI: 4.75% Traditional ROI: 3.41%
917 BRANTLEY DRIVE Longwood, FL Under contract-accepting backup offers. Beautifully updated 4-bedroom, 2.5-bath home in on...	4 beds \| 3 baths \| 2,413 sq.ft.	$500,000	Airbnb cash on cash: 7.07% Traditional cash on cash: 4.26% Airbnb Rental Income: $5377 Traditional Rental Income: $2976 Airbnb ROI: 7.07% Traditional ROI: 4.26%
470 S PIN OAK PLACE #312 Longwood, FL Bright, Updated Condo with Pond Views in A-Rated Seminole County School District! Welcome...	1 beds \| 1 baths \| 823 sq.ft.	$175,000	Airbnb cash on cash: 0.69% Traditional cash on cash: 3.42% Airbnb Rental Income: $1304 Traditional Rental Income: $1352 Airbnb ROI: 0.69% Traditional ROI: 3.42%
851 N WAYMAN STREET Longwood, FL Welcome to this beautifully updated Longwood pool home full of charm, warmth, and timeless...	3 beds \| 2 baths \| 1,353 sq.ft.	$362,500	Airbnb cash on cash: 5.83% Traditional cash on cash: 4.85% Airbnb Rental Income: $3221 Traditional Rental Income: $2160 Airbnb ROI: 5.83% Traditional ROI: 4.85%
430 BRASSIE DRIVE Longwood, FL This 4-bed 3 bathroom home in Longwood offers multi-generational flexibility, over 2,500 s...	4 beds \| 3 baths \| 2,537 sq.ft.	$550,000	Airbnb cash on cash: 6.78% Traditional cash on cash: 4.61% Airbnb Rental Income: $5377 Traditional Rental Income: $3177 Airbnb ROI: 6.78% Traditional ROI: 4.61%
572 LAKE WILDMERE COVE Longwood, FL Here is your opportunity to own a true Turn Key Investment property.This almost new townho...	4 beds \| 5 baths \| 2,294 sq.ft.	$455,000	Airbnb cash on cash: 6.54% Traditional cash on cash: 4.01% Airbnb Rental Income: $5377 Traditional Rental Income: $3213 Airbnb ROI: 6.54% Traditional ROI: 4.01%
115 FOREST POINT LANE Longwood, FL Under contract-accepting backup offers. Welcome to 115 Forest Point Lane â a beautifully...	4 beds \| 3 baths \| 2,689 sq.ft.	$875,000	Airbnb cash on cash: 3.65% Traditional cash on cash: 2.61% Airbnb Rental Income: $5377 Traditional Rental Income: $3443 Airbnb ROI: 3.65% Traditional ROI: 2.61%
328 ISLAND SOUND COURT Longwood, FL Welcome to this stunning 5-bedroom, 4-bathroom energy-efficient Pulte home located in a de...	5 beds \| 4 baths \| 3,715 sq.ft.	$1,050,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.15% Airbnb Rental Income: $null Traditional Rental Income: $4310 Airbnb ROI: N/A Traditional ROI: 2.15%
223 ROYAL OAKS CIRCLE Longwood, FL MOTIVATED SELLERS will consider all reasonable offers! IMPROVED PRICE! One of the BEST VA...	4 beds \| 2 baths \| 2,842 sq.ft.	$575,000	Airbnb cash on cash: 6.64% Traditional cash on cash: 3.7% Airbnb Rental Income: $5377 Traditional Rental Income: $2711 Airbnb ROI: 6.64% Traditional ROI: 3.7%
1510 PELICAN STREET Longwood, FL 3-bed, 2-bath residence nestled on a serene, tree-lined street in one of Longwoodâs DESI...	3 beds \| 2 baths \| 1,269 sq.ft.	$268,900	Airbnb cash on cash: 6.8% Traditional cash on cash: 4.74% Airbnb Rental Income: $3221 Traditional Rental Income: $1973 Airbnb ROI: 6.8% Traditional ROI: 4.74%

Real Estate investment in Longwood, FL

There are 133 properties for sale in the city of Longwood . The median list price in Longwood is $427,700 and the average price per square foot is $208. In November 2025, the average monthly cash on cash return in Longwood is 4.00%. The average monthly rental income in Longwood is $2,210.

Longwood, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 133 investment properties available for sale in Longwood.

In 2025, the best neighborhood to buy investment property is Longwood.

The ROI for Short-Term is higher than the Long-Term in Longwood with average rental income of $3,221.

Your search for investment property begins and ends here

Investment Property for Sale in Longwood, FL

3996 RADLEY COURT #3996

Longwood, FL

2 beds | 2 baths | 1,427 sq.ft.

$280,000

Airbnb cash on cash: -1.51%

Traditional cash on cash: 3.22%

Airbnb Rental Income: $1115

Traditional Rental Income: $1988

Airbnb ROI: -1.51%

Traditional ROI: 3.22%

4102 CLUBSIDE DRIVE #4102

Longwood, FL

2 beds | 3 baths | 1,380 sq.ft.

$232,900

Airbnb cash on cash: -1.29%

Traditional cash on cash: 3.95%

Airbnb Rental Income: $1115

Traditional Rental Income: $1894

Airbnb ROI: -1.29%

Traditional ROI: 3.95%

3235 WINDING PINE TRAIL

Longwood, FL

4 beds | 6 baths | 4,262 sq.ft.

$1,400,000

Airbnb cash on cash: 1.1%

Traditional cash on cash: 3.79%

Airbnb Rental Income: $5377

Traditional Rental Income: $7787

Airbnb ROI: 1.1%

Traditional ROI: 3.79%

211 FAIRWAY DRIVE #211

Longwood, FL

3 beds | 2 baths | 1,496 sq.ft.

$187,500

Airbnb cash on cash: 7.73%

Traditional cash on cash: 5.4%

Airbnb Rental Income: $3221

Traditional Rental Income: $2080

Airbnb ROI: 7.73%

Traditional ROI: 5.4%

899 LORMANN CIRCLE

Longwood, FL

3 beds | 2 baths | 969 sq.ft.

$289,990

Airbnb cash on cash: 7.38%

Traditional cash on cash: 4.84%

Airbnb Rental Income: $3221

Traditional Rental Income: $1803

Airbnb ROI: 7.38%

Traditional ROI: 4.84%

199 E MARVIN AVENUE

Longwood, FL

3 beds | 1 baths | 967 sq.ft.

$265,000

Airbnb cash on cash: 7.76%

Traditional cash on cash: 4.53%

Airbnb Rental Income: $3221

Traditional Rental Income: $1686

Airbnb ROI: 7.76%

Traditional ROI: 4.53%

112 CROWN OAKS WAY #112

Longwood, FL

2 beds | 2 baths | 1,119 sq.ft.

$130,000

Airbnb cash on cash: -4.32%

Traditional cash on cash: 3.69%

Airbnb Rental Income: $1115

Traditional Rental Income: $1741

Airbnb ROI: -4.32%

Traditional ROI: 3.69%

2681 AZALEA DRIVE

Longwood, FL

3 beds | 2 baths | 1,399 sq.ft.

$365,000

Airbnb cash on cash: 4.94%

Traditional cash on cash: 3.48%

Airbnb Rental Income: $3221

Traditional Rental Income: $1994

Airbnb ROI: 4.94%